Dimethyl Sulfoxide → HCID 178433637, compound

HRID 2271112Notes

Reaction equation

HRID 2271112 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:10]([C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[N:17]=3)=[CH:11][NH:12][C:13]=2[CH3:14])[CH:5]=[CH:6][CH:7]=1.CN(C)/[CH:28]=[N:29]/[N:30]=[CH:31]/N(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.CS(C)=O>C1(C)C=CC=CC=1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:16]2[C:15](=[O:25])[C:10]3=[CH:11][NH:12][C:13]([CH3:14])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([N:1]5[CH:31]=[N:30][N:29]=[CH:28]5)[CH:3]=4)[C:9]3=[N:17]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6101p-Toluenesulfonic acid2×HCID 9613942N'-((Dimethylamino)methylene)-N,N-dimethylformohydrazonamideHCID 178433638HCID 178433638, compound

Product 1

HCID 178433637HCID 178433637, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7-(3-aminophenyl)-2-(4-chlorophenyl)-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one (0.100 g, 0.285 mmol), N,N-dimethylformamide azine (Bartlett, R. K.; Humphrey, I. R. J. Chemn. Soc. C 1967, 1664) (41.3 mg, 0.290 mmol), and p-toluenesulfonic acid (10 mg, 0.053 mmol) in toluene (4 ml) was heated at reflux under nitrogen for 7 days, adding more p-toluenesulfonic acid (10 mg, 0.053 mmol) and some DMSO after 1 day. The solvents were removed in vacuo and the residue was purified by flash chromatography (silica gel, 5-15% MeOH/CH2Cl2), then trituration in hot MeOH-CH2Cl2, to leave 0.0436 g (38%) of the title compound as a yellow solid; mp >350° C.; 1H NMR (360 MHz, DMSO-d6) δ2.29 (3H, s), 7.41 (2H, d, J 9.1 Hz), 7.59 (1H, d, J 7.7 Hz), 7.70 (1H, t, J 7.7 Hz), 7.79 (1H, dd), 7.87 (1H, fine t), 8.11 (2H, d, J 8.9 Hz), 8.62 (1H, s), 9.18 (2H, s), 12.52 (1H, br s); MS (ES+) m/z 403/405 1MH]+. Anal. found: C, 61.14; H, 3.79; N, 20.29. C21H15ClN6O.0.5H2O requires: C, 61.24; H, 3.92; N, 20.41%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 7 days
  3. customThe solvents were removed in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, 5-15% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fd1ac3e914f1428aa856ff0b69f47b26
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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